A THREE-COMPONENT SYNTHESIS OF TRIFLUOROMETHYLATED HEXAHYDROPYRROLO[1,2-<i>a</i>]IMIDAZOL-5-ONES AND HEXAHYDROPYRROLO[1,2-<i>a</i>]PYRIMIDIN-6-ONES

Authors

  • Марина В. Горяева Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137
  • Олеся А. Фефелова Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137
  • Янина В. Бургарт Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137
  • Марина А. Ежикова Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137
  • Михаил И. Кодесс Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137
  • Павел А. Слепухин Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137
  • Галина А. Триандафилова Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990
  • Сергей Ю. Солодников Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990
  • Ольга П. Красных Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990
  • Виктор И. Салоутин Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

DOI:

https://doi.org/10.1007/6850

Keywords:

diamines, dipyrrolo[1, 2-a, 2', 1'-b]imidazole-3, 8-dione, 1'-b]pyrimidine-3, 9-dione, ethyl trifluoropyruvate, hexahydropyrrolo[ 1, 2-a]imidazol-5-ones, hexahydropyrrolo[1, 2-a]pyrimidin-6-ones, methyl ketones, analgesic activity, three-component reaction

Abstract

A three-component reaction of ethyl trifluoropyruvate, methyl ketones, and ethylenediamine or 1,3-diaminopropane afforded hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones. When using an excess of ethyl trifluoropyruvate in reactions with acetone and diamines, dipyrrolo[1,2-a:2',1'-b]imidazole-3,8-dione and dipyrrolo[1,2-a:2',1'-b]pyrimidine-3,9-dione were obtained. An aldol mechanism for the formation of the bi- and tricyclic compounds was proposed, and their diastereomeric structure was established. Some of the obtained heterocycles were found to possess analgesic activity.

Authors: Marina V. Goryaeva, Olesya А. Fefelova, Yanina V. Burgart, Marina А. Ezhikova, Mikhail I. Kodess, Pavel А. Slepukhin, Galina А. Triandafilova,
Sergey Yu. Solodnikov, Olga P. Krasnykh, Victor I. Saloutin*

Author Biographies

Марина В. Горяева, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

старший научный сотрудник лаборатории фторорганических соединений, к.х.н.

Олеся А. Фефелова, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

старший лаборант-исследователь лаборатории фторорганических соединений

Янина В. Бургарт, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

зам. директора ИОС УрО РАН, ведущий научныйй сотрудник лаборатории фторорганических соединений, д.х.н., профессор

Марина А. Ежикова, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

научный сотрудник группы ИК и ЯМР спектроскопии

Михаил И. Кодесс, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

руководитель группы ИК и ЯМР спектроскопии, к.х.н.

Павел А. Слепухин, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

руководитель группы рентгеноструктурного анализа, к.х.н.

Галина А. Триандафилова, Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990

младший научный сотрудник

Сергей Ю. Солодников, Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990

научный сотрудник

Ольга П. Красных, Perm National Research Polytechnic University, 29 Komsomolsky Ave., Perm 614990

доцент, к.х.н.

Виктор И. Салоутин, Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620137

заведующий лабораторией фторорганических соединений, д.х.н., профессор, член-корр. РАН

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Published

2022-09-20

Issue

Vol. 58 No. 8/9 (2022)

Section

Original Papers